(−)-(2R,1′R)-2-((bromobenzoyl)oxy-(4-nitrophenyl)methyl)cyclohexan-1-one | 1523213-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (−)-(2R,1′R)-2-((bromobenzoyl)oxy-(4-nitrophenyl)methyl)cyclohexan-1-one
• 英文别名: (-)-(2R,1′R)-2-((bromobenzoyl)oxy-(4-nitrophenyl)methyl)cyclohexan-1-one
• CAS: 1523213-15-1
• 化学式: C₂₀H₁₈BrNO₅
• 分子量: 432.271
• InChiKey: ZOZOYOBCUPORQN-HKUYNNGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  86.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-溴苯甲酰氯 、 2-(hydroxy(4-nitrophenyl)methyl)cyclohexan-1-one 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 31.0h， 以45%的产率得到(−)-(2R,1′R)-2-((bromobenzoyl)oxy-(4-nitrophenyl)methyl)cyclohexan-1-one
  参考文献：
  名称：

  Asymmetric aldol reactions between cyclic ketones and benzaldehyde catalyzed by chiral Zn2+ complexes of aminoacyl 1,4,7,10-tetraazacyclododecane: effects of solvent and additives on the stereoselectivities of the aldol products

  摘要：

  The direct aldol reaction between cyclic ketones and 4-nitrobenzaldehyde catalyzed by chiral Zn2+ complexes of aminoacyl 1,4,7,10-tetraazacyclododecane is reported. The anti-aldol products were mainly formed in cyclohexanone/N-methylpyrrolidone(NMP)/MeOH with good diastereo- and enantioselectivity, while syn-aldol adducts were obtained as major products with good enantioselectivity in cyclohexanone/H2O and cyclohexanone/NMP/H2O. The fact that the UV/vis spectra of 2,6-dipheny1-4-(2,4, 6-triphenyl-1-pyridinio)phenolate (Reichardt's dye) were nearly identical in these solvent systems suggests that the switch in the relative configuration of the aldol products is induced by a large excess of H2O rather than the polarity of the solvent system. Furthermore, the addition of a small amount of TFA improved the enantioselectivity of the syn-aldol adducts produced in cyclohexanone/H2O with up to 92% ee (anti/syn ratio = 30:70). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.10.009